Dimethylformamide → Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-

HRID 552928

反応式

HRID 552928 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].[CH3:16][N:17](C)C=O.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O.[C-]#N.[Zn+2].[C-]#N.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:14][N:13]([CH3:15])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:16]#[N:17])[CH:3]=2)[NH:7][CH:6]=1

参加物

8

反応物 3

HCID 6228DimethylformamideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 3602525-Bromo-N,N-Dimethyltryptamine

生成物 1

HCID 28511Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23994Zinc触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

実験手順

[2-(5-Bromo-1H-indol-3-yl)-ethyl]-dimethylamine (16) (500.0 mg, 1.872 mmol) (U.S. Pat. No. 5,998,438) was placed in an argon purged oven dried flask fitted with a stirbar. Zinc cyanide (395.0 mg, 3.368 mmol, 1.8 equivalents); Zinc powder (14.7 mg. 0.225 mmol, 0.12 equivalents) and tris(dibenzylideneacetone)dipalladium(0) (42.9 mg, 0.0468 mmol, 0.025 equivalents) were added sequentially followed by anhydrous N,N-dimethylformamide (15 mL). A solution of tri-t-butylphosphine in hexanes (10 wt %, 189.0 mg, 280 μl, 0.05 equivalents) was added and the mixture was stirred for 15 minutes at room temperature and then heated in an oil bath at 60° C. for 30 minutes. After cooling to room temperature the mixture was transferred into a separatory funnel and diluted with distilled water (15 mL). The aqueous phase was extracted with ethyl acetate (3×30 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was purified via silica gel column chromatography (10% 2M NH3 in methanol/90% dichloromethane) to provide 3-(2-(dimethylamino)ethyl)-1H-indole-5-carbonitrile (57) as a yellow residue (150 mg, 37.6% yield). 1H NMR (DMSO) δ: 2.21 (s, 6H), 2.54 (m, 2 H), 2.84 (t, 2H), 7.36-7.41 (m, 2H), 7.49 (d, 1H), 8.07 (s, 1H), 11.38 (br s, 1H).

後処理

  1. custom5,998,438) was placed in an argon purged oven
  2. customdried flask
  3. customfitted with a stirbar
  4. temperatureheated in an oil bath at 60° C. for 30 minutes
  5. temperatureAfter cooling to room temperature the mixture
  6. customwas transferred into a separatory funnel
  7. extractionThe aqueous phase was extracted with ethyl acetate (3×30 mL)
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified via silica gel column chromatography (10% 2M NH3 in methanol/90% dichloromethane)

出典と根拠

ORDレコード
ord-bfc91ec2bd584afdbc53c0e97058eae5
出典データセット
uspto-grants-2011_05
特許番号
US07951940B2

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